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Merck
CN

855790

O,O-Diethyl O-(4-nitrophenyl) phosphate

technical grade, 90%

Synonym(s):

Diethyl p-nitrophenyl phosphate, Paraoxon, Paraoxon-ethyl

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About This Item

Linear Formula:
O2NC6H4OP(O)(OC2H5)2
CAS Number:
311-45-5
Molecular Weight:
275.20
EC Number:
206-221-0
UNSPSC Code:
12352103
PubChem Substance ID:
329769389
Beilstein/REAXYS Number:
1915526
MDL number:
MFCD00007316

Key Documents

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InChI key

WYMSBXTXOHUIGT-UHFFFAOYSA-N

InChI

1S/C10H14NO6P/c1-3-15-18(14,16-4-2)17-10-7-5-9(6-8-10)11(12)13/h5-8H,3-4H2,1-2H3

SMILES string

CCOP(=O)(OCC)Oc1ccc(cc1)[N+]([O-])=O

grade

technical grade

assay

90%

form

liquid

impurities

≤10% 4-nitrophenol

refractive index

n20/D 1.51 (lit.)

density

1.274 g/mL at 25 °C (lit.)

functional group

nitro, phosphate

Biochem/physiol Actions

Potent irreversible acetylcholinesterase inhibitor

pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

signalword

Danger

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 1 Oral - Aquatic Acute 1 - Aquatic Chronic 1

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
05988MW
15331EN
08346BZ
07337MF
05534JX

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Krystle L Yozzo et al.
Aquatic toxicology (Amsterdam, Netherlands), 126, 346-354 (2012-10-11)
Using paraoxon as a reference acetylcholinesterase (AChE) inhibitor, the objective of this study was to develop an adverse outcome pathway (AOP) that provided quantitative linkages across levels of biological organization during zebrafish embryogenesis. Within normal zebrafish embryos, we first demonstrated
Francesca Cavalieri et al.
ACS applied materials & interfaces, 5(2), 464-471 (2012-12-26)
Air-filled lysozyme microbubbles (LSMBs) were engineered as a support for the immobilization of gold nanoparticles and an enzyme, alkaline phosphatase, in order to develop micro-antimicrobial and biosensing devices. Gold nanoparticles immobilized on LSMBs significantly improved the antimicrobial efficacy of the
Aino Salminen et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 29(4), 1435-1445 (2015-01-01)
Various cell types in atherosclerotic lesions express matrix metalloproteinase (MMP)-8. We investigated whether MMP-8 affects the structure and antiatherogenic function of apolipoprotein (apo) A-I, the main protein component of HDL particles. Furthermore, we studied serum lipid profiles and cholesterol efflux
J Allen Crow et al.
Biochemical pharmacology, 84(9), 1215-1222 (2012-09-05)
Carboxylesterase type 1 (CES1) and CES2 are serine hydrolases located in the liver and small intestine. CES1 and CES2 actively participate in the metabolism of several pharmaceuticals. Recently, carbamate compounds were developed to inhibit members of the serine hydrolase family
Tamara C Otto et al.
Chemico-biological interactions, 203(1), 186-190 (2012-10-09)
In an effort to discover novel catalytic bioscavengers of organophosphorus (OP) nerve agents, cell lysates from a diverse set of bacterial strains were screened for their capacity to hydrolyze the OP nerve agents VX, VR, and soman (GD). The library
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